I hear ya man....thank god he's past those days- he's 20 now, my only one left at home my 2 daughters are off and gone to college, he chose a different path and started his own small business, and is now actually a sub-contractor for the company I work for, and he's still working on his degree nights and making decent money so he buys his own toys now.
No one here is saying "dont upgrade". Its just, as it stands, he has a lot of hooch in his ivy bridge build and the benefits he gets from an upgrade wont really be dramatic for the money. Looking at spending 600$ to get 15% in performance. Its just not overly prudent I suppose.
An option though, he may still get a chunk of money back for the 3770k rig. If he can find a buyer for his stuff, then yeah he should absolutely jump on the skylake bandwagon.